Stannous chloride dihydrate → HCID 178428296, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tin (II) chloride dihydrate (600 mg, 4.43 mmol) in concentrated hydrochloric acid (1 mL), 9.04 mmol) was cooled below 10° C. A solution of 6-(4-methylpiperazin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)-5-nitro-2-[(E)-2-phenylvinyl]pyrimidin-4-amine (Example 4, 400 mg, 0.95 mmol) in methanol (20 mL) was added dropwise to the reaction mixture. The reaction was allowed to come to ambient temperature and was then heated to 60° C. for 3 hours. Progress of the reaction was monitored by TLC. The reaction mixture was reduced to ⅓rd volume of the original volume under vacuum. The residue was diluted with ethyl acetate (40 mL) and 1N NaOH (20 mL) was added to the reaction mixture. The organic layer was separated, dried and the solvent evaporated under reduced pressure. The residue was then triturated with ethyl acetate and hexane to afford 6-(4-methylpiperazin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)-2-[(E)-2-phenylvinyl]pyrimidin-4,5-diamine as a yellow solid (200 mg). 1H NMR (400 MHz, DMSO-d6): δ 7.94 (br, 1H), 7.70 (d, 1H, J=16 Hz), 7.59 (m, 2H) 7.38 (m, 2H), 7.29 (m, 1H), 7.05 (d, 1H, J=16 Hz), 6.36 (br, 1H), 3.44 (br, 2H), 3.3 (br, 4H), 2.59 (br, 4H), 2.36 (s, 3H), 2.33 (s, 3H). MS (m/z) 391 (M+1).

Provenance & Evidence